Wenger's (1998) concepts "community of practice," "brokering," and "transfer" explain the challenges co-operative (co-op) education students face in relating the knowledge learned in school with what they learn while participating as members of a workplace. The research for this paper is set within the contexts of the knowledge economy and increased collaboration in the workplace. The paper draws on several qualitative studies of work-based education to examine the similarities and differences between learning in the workplace and learning in school, with a focus on science education and science-rich workplaces. Barriers to connecting school knowledge and workplace knowledge include the nature of science (its purpose, accountability, and substance), the structure of knowledge in each setting, the form content knowledge takes, the sequence that the curriculum is presented in, and the gatekeeping that occurs when knowledge is accessed. The paper addresses implications for interventions in school and the workplace, with attention to the transition from school to work, and concludes by pointing to profound obstacles to connecting school knowledge with workplace knowledge.